The Craziest Flight Itinerary in the World

Anyone who travels by air has experienced this disorienting sensation: you’re searching online for the lowest fare from Point A and Point B when up pop some truly wacky flight routings. On a trip from Cleveland to New York City, for example—nonstop, about an hour flight—one online travel agency came up with a punishing, 21-hour odyssey that would have had me cooling my heels in Fort Lauderdale overnight, hence erasing the $100 savings over a more direct routing (unless I wanted to sleep on the airport floor). The display screen actually read “good choice!” next to this trip from hell. Another site would have sent me flying in circles—literally—to Chicago, then Philly, up to Boston, before landing in my actual destination ten hours later.

Of course, we assume that no one in their right mind would choose these options, even to save a few bucks. But why are they even being offered to begin with? And does anyone ever hit the buy button for one of these bizarre itineraries? Actually, yes: we know of at least one person who not only booked one, but actually withstood the entire journey. Boston-based software developer Rafael Mendiola stumbled on one such ridiculous flight itinerary as he was searching for flights to San Francisco, and thought, “Wouldn’t it be funny if someone actually took this flight?”

“It had five stops, and the total duration was almost 24 hours," he says. "I thought, 'This is the very definition of insanity.' Of course, I immediately volunteered for the flight."

This might sound like a reality TV stunt, but in fact, Mendiola is an MIT-trained computer whiz who works for the new business travel app Lola, which uses artificial intelligence to generate custom flight and hotel options, based on past bookings and other information customers provide in their profiles. His boss? None other than Paul English, best known as a founder of meta-search site Kayak.com.

In an interview, Mendiola shared details of this manic marathon. “It began at 5 a.m., when we had to leave home to get to Logan Airport for the first flight, Southwest Airlines, to Denver.” (To share the misery, Mendiola was traveling with his girlfriend.) That nearly five-hour flight was the easy part, he said. After that, he continued on the same plane to his next pit stop, San Antonio, where he had a nearly three-hour layover before boarding another plane bound for New Orleans. Then it was on to Phoenix, where he had an hour to kill before heading to Las Vegas.

Mendiola had just enough time to play the slot machines before it was on to his final leg to San Francisco. It was nearly midnight when the travelers finally emerged from the airport. “We immediately got a massage—we were hurting,” Mendiola jokes.

A quick calculation shows the exact tab for the pain: Total airfare: $669.56 per person. Total miles flown: 5,002, or roughly 2,300 more miles than a direct flight. In-flight meals consumed: 0. Time spent in the air: 14.5 hours. Time spent inside airports: more than seven hours.

Mendiola's itinerary, mapped.

Google Maps

The trip was booked via Concur, the popular business travel management booking and management tool, and the flight itinerary was entirely on Southwest. But English says it’s not fair to blame either of those companies for this trip—in fact, you could find plenty of similar ones on any number of airline or OTA sites like Priceline and CheapoAir. And Southwest’s roots as a short-haul, one-class airline means that it largely avoids long-haul nonstops, so its customers are more accustomed to making multiple stops.

Still, what does a travel tech guru really think is going on here?

“It’s one of these cases where it’s a bad algorithm or bad AI,” English says. “It’s looking at every possible way to go to San Francisco, and whether the price is right. They don’t really think about traveler pain."

But you don’t need a PhD from MIT to figure out that you don’t want to put someone through these incredible hoops just to save money—and, in fact, the airfare for this loopy trip wasn’t even a bargain.

Southwest Airlines declined our request to comment for the record. But a source at the airline speaking on background noted that while this trip may have been extreme, “there have always been some people willing to take less convenient routings because it costs less.” William McGee, a consumer advocate and author of the book Attention All Passengers, says it’s just a symptom of an airline booking system that’s so complex and confusing it’s out of control. “Unfortunately, the better the technology gets, the worse it gets for consumers,” he says. While the companies behind the technology are focused on speed and the sheer volume of information they deliver to consumers, the resulting cacophony is a turn-off for customers, he says.

In fact, McGee said he did an investigation of this when he was editor of Consumer Reports Travel Letter more than 15 years ago. “We called it nonsensical routings. You’d ask for the lowest fare between New York and Los Angeles, and you’d get results with four stops and multiple carriers.” Of course, users can filter out the most ridiculous ones, but McGee says that consumers ultimately get screen fatigue. “You have to wonder why they don’t just weed out these routings. Or are these low fares just a way to bring you into the showroom?"